Tips for Traveling With Your Boss

Traveling with your boss? Even if you’re headed somewhere warm and exotic, don’t think of it as a vacation.

“Even though you’re not in your actual office, you are still at work,” says Anna Post, who teaches business etiquette seminars at the Emily Post Institute in Burlington, Vermont. “Everything that applies in the office applies on the road.”

That means showing up on time for a 6am cross-country flight dressed the way you’d be dressed for a day at the office and not looking ready to snooze your way across the country.

And be prepared for longer days and nights when you’re traveling with the boss. You may be asked to take a client to dinner, or to have dinner or drinks with your boss and a client. It’s essential to be available and gracious in this situation, Post says.

“You want to be prepared for this in advance,” she says. “Know that you may have your evenings cut into when you are traveling with the boss. Your work day may not end at 6pm when you are on the road. It’s always a good idea to review these plans with your boss ahead of time so there aren’t any unpleasant surprises.”

The good news? Your boss should be picking up the tab for drinks and dinner. “Typically, the most senior person pays,” Post says. “Occasionally when you get into very high ranks, the boss may not handle money at all and then you would pay the check on their behalf, but this is rare.”

If the check’s sitting on the table and the boss shows no signs of picking it up, it’s perfectly acceptable for you to ask if he or she would like for you to put it on your credit card, Post says.

Whether you’re dining with the boss or not, it is crucial that you be on time for every part of your trip together, explains travel planner Nadine Nardi Davidson, author of “Travel with Others Without Wishing They’d Stayed Home.”

“Even if you’re the kind of hang-loose traveler who typically gets to the airport at the last minute, don’t leave the boss pacing at the gate wondering if you’re going to miss the flight,” she says. “Promptness is critical. And don’t check baggage. That way you won’t be the one holding the others up with the wait in baggage claim.”